If you are to run a quick Google search of “Winston Churchill” and view the image results, you are going to find two dominant results: A black and white photo of him sitting with his serious expression and a smiling Churchill with a fat cigar sticking out his mouth. As one of the most important political figures of the 20th century, Churchill did not only become famous for his oratorical skills and political leadership in the United Kingdom, especially during the war, but also for his trademark image of being a devoted smoker. A dangerous habit justified by the challenges that he had to face throughout his life and career.

A Habit That Started From a Young Age

Churchill was born to an A-list family on 30 November 1874: His dad was a politician and Parliament member, while his American mom was the daughter of a rich stockbroker, financier, and newspaper proprietor in New York. He would grow to admire the political successes of his dad, although their relationship would not be an easy one. On the other hand, his mom would not be able to provide her young son with the attention he yearned for.

Winston Churchill at Harrow School, 1892. (International Churchill Society)

As a student, he had to attend multiple boarding schools before barely passing his entrance exams for Harrow, one of Britain’s most elite schools. Soon, his parents would discover that not only was he not interested in studying, but he would also begin to smoke cigarettes with his classmates. His mother’s solution was to bribe him: She promised her son that she would give him a pony and a pistol if he stopped smoking and instead focused on school.

Discovering His Cuban Treasure

In 1895, just after graduating from the Royal Military Academy Sandhurst, Churchill was eager to put his name out there and gain experience, so he and a fellow officer visited Cuba as an observer of the ongoing conflict between the Cuban rebels and the Spanish colonialists. While there, and just like many other English officers of that time, he wanted to explore the attractions and delicacies that Cuba could offer, and that was how he found out about the love of his life: Cuban cigars.

Cigars have always been Cuba’s leading export product. He would specifically love two specific Cuban cigars: Romeo y Julieta and La Aroma de Cuba. Two brands that would turn him into a full-pledge and dedicated smoker. So dedicated that in his home in Kent, the Chartwell Manor, he had some 3,000 to 4,000 of these cigars stacked in his study room, where they were organized and categorized by size, brand, and packaging.

Romeo Y Julieta Churchill Cigars. (The original uploader was Geographer at English Wikipedia.CC BY 2.5, via Wikimedia Commons)

Since then, until he rose to power, his friends and associates would regularly send him shipments of his Cuban cigars, ensuring he had access to them and that he could smoke his usual 8 to 10 sticks per day. Churchill’s vice was not cheap, too. As one of his valets, Roy Howells, wrote a book about his service with the Prime minister, he confessed,

It took me a little while to get used to the fact that in two days his cigar consumption was the equivalent of my weekly salary.

This only proved how much money he was willing to spend for the love of his Romeo y Julieta and La Aroma de Cuba.

A Special Mask

It seemed like nothing could stop and take the Prime Minister’s cigars away from him, not even flying at an altitude of 15,000 feet. At one time during World War II, Churchill needed to travel by air on a high-altitude flight in an unpressurized cabin. This meant that he had to wear a special flight suit that included an oxygen mask, which meant that he could not smoke for a few hours. It doesn’t sound so bad, right? Apparently, not for Churchill as for him, it was simply not acceptable.

Just the evening before his trip, he requested that a special oxygen mask be made for him that would allow him to smoke while he was 15,000 feet above. He was Winston Churchill, so it was no surprise that his wish was no question granted. The next day, Churchill flew in a mask with a hole through which he could insert his beloved cigar and smoke as he pleased.  We aren’t sure that an oxygen mask with thumb-sized hole in it is still a functioning mask though.

No one had the sense(or the temerity) to warn the Prime Minister that an open flame near a source of pure oxygen flowing under pressure could prove to be an explosive and fatal combination for him.